


Tainted

by HazelDomain



Category: Supernatural
Genre: Anal Sex, Ass Play, Bunker Sex, Castiel's First Time, Claiming, Come Marking, Comeplay, Dean is dommy, Dirty Talk, Established Dean Winchester/Sam Winchester, First Time, Fuck Or Die, M/M, Manhandling, Multi, Rimming, Sam is hung, Size Kink, Spitroasting, Sub Sam Winchester, Switch Castiel, Switch Dean, Switch Sam Winchester, Threesome - M/M/M, Voyeur Dean, Voyeurism, jizz everywhere, sinning
Language: English
Status: Completed
Published: 2017-02-01
Updated: 2017-02-05
Packaged: 2018-09-21 09:16:19
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 5,820
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9541202
Author URL: https://archiveofourown.org/users/HazelDomain/pseuds/HazelDomain
Summary: Heaven's under new management. They want all their angels reporting home for retraining.Sam and Dean aren't letting Cas go that easily.





	1. Chapter 1

**Author's Note:**

> Doing something a little different for this one. 
> 
> I've got three prompts that kinda stuck together in my head. 
> 
> Main prompt: http://spnkink-meme.livejournal.com/116811.html?thread=42524491#t42524491 
> 
> Sub-prompt chapter 1: http://spnkink-meme.livejournal.com/116811.html?thread=42594379#t42594379
> 
> Sub- prompt chapter 2: http://spnkink-meme.livejournal.com/116811.html?thread=42591563#t42591563 
> 
>  
> 
> Note: I haven't been Catholic for ten years so I have no skin in this game, but if you're triggered by the idea that kinkiness keeps you outta heaven, this is not your fic.

“I didn’t  _ make _ the rules,” Gabriel muttered, shrugging. “I’m just telling you how it is.” 

“I’m calling bullshit,” Sam snapped, rolling his eyes at the archangel. “If heaven was on the mend, we’d have heard something about it by now.”

“Right?” Dean added, glancing to the side, where Cas was shifting uneasily. “ _ Right, _ Cas?” 

“There have been… rumors,” the seraph answered, looking up to meet Dean’s eyes. “But there have been rumors before. I didn’t want to say anything until things looked more certain.” 

“Congrats, bro, they’re certain,” Gabe announced, clapping him on the shoulder. “Time to go home and face the music, buddy-boy.” 

“No. He’s not going,” Dean objected, as a look of sick terror crossed Cas’s face. “Not after what they did to him last time.” 

“I don’t have a choice,” Cas mumbled, glancing to Gabe for verification. “If heaven is calling the ranks to order, they’ll stop at nothing to bring divergent soldiers back into line.” 

“There has to be some way to hide you from them, some kind of warding,” Dean started, but Sam interrupted him, frowning at Gabe. 

“If they’re calling everyone back to heaven, then what are  _ you _ doing down here?” 

Gabe laughed, rolling his eyes. 

“ _ Me? _ Listen bucko, I barely even  _ count _ as an angel any more. Turns out, when you spend a thousand years marauding as a pagan god, heaven’s more than happy to keep your grubby little toes off the carpet.” He raised an eyebrow. “I’ve got sex acts named after me, nobody up top even wants to admit we’re related.” 

“What about the reaper?” Cas asked, looking up. “I’ve engaged in intercourse. Was that enough to sully my grace?” 

Gabe rolled his eyes. 

“Please. Sex with  _ one _ woman? Missionary? In the  _ dark? _ Dude, you didn’t even use a condom-” 

“Alright alright, we get the point,” Dean interrupted, wrinkling his nose. “Nobody needs those details, Gabe. So what do we do, take him to a Tijuana show?”

“Not unless he plans on participating,” Gabe answered, not looking like he was discarding the idea. “But that would probably do it, yeah.” 

“We’re not doing that,” Sam snapped, just as Cas was opening his mouth to ask what a Tijuana show was. “It doesn’t need to be that, specifically, right?” 

“It likely won’t even require intercourse,” Cas answered, frowning. “Any sort of profoundly unbiblical activities should be sufficient to place a stain upon my grace.” 

“Profoundly unbiblical?” Dean asked, skeptical. Cas nodded, counting off on his fingers. 

“Failure to contain a savage bull, selling a man into slavery, consumption of human flesh-” 

“We’re not doing that,” Dean interjected. Gabe looked like he was going to say something, but instead just shrugged. Cas continued his list. 

“Perjury, murder, practicing divination, coercing a daughter into prostitution…” he frowned, then shook his head. “Jimmy’s vessel is already circumcised but the crushing of the testicles would prevent entrance into the congregation-”

“Well, that’s my cue to go. Have fun figuring this one out,” Gabe interrupted. He winked at Sam and was gone a few seconds later. Sam muttered something about making the wards on the bunker stronger. Cas continued his list of sins, seemingly not noticing. Sam and Dean glanced at each other, a silent conversation passing between them. 

“What about incest?” Dean asked after a minute. Cas frowned, considering. 

“Most likely, but that would require intercourse with another angel or a close relative of Jimmy’s, and I don’t think I’m likely to make much progress on that front.” 

Dean looked to Sam, pleading. 

“I think he means having sex with siblings,” Sam clarified. “Brothers, maybe?” 

Cas nodded, still thinking. 

“Homosexuality and incest are both forbidden in the old testament, so the combination of the two would likely go a long way toward achieving expulsion from heaven’s army.”

“What if it was like,  _ really _ filthy?” Dean added, maybe a little too hopefully. Sam glared at him, and Dean made a helpless gesture. Cas didn’t notice. 

“I suppose it would be worth a shot, but that only compounds the difficulty of finding a willing partner,” Cas answered. He was looking at Dean now, like there was something in Dean’s expression he was having trouble interpreting. Dean was grinning like an idiot. Sam cleared his throat. 

“Cas, if you’d be willing, Dean and I-”

“No,” Cas interrupted, looking firmly at Sam and missing Dean’s crestfallen look. “The bond between the two of you is perfect and beautiful, I would never ask you to compromise it for my sake.” 

“What, you think we’ll get jealous over you?” Dean asked, raising his eyebrows. Castiel shook his head. 

“When I slept with April, the way I felt about her afterwards was so different, so fundamentally  _ intimate _ ... I don’t think I could ever have gone back. I would never ask you to alter your relationship in that way.”

“You think we’ll feel different after we have sex?” Sam asked, confused, and Castiel nodded sagely. Sam glanced to Dean, who shrugged. 

“Cas… listen, Dean and I…” Sam trailed off, unsure of how to proceed. He glanced back to Dean. Dean shrugged again, but before Sam could turn back to Cas, his brother had grabbed him by the lapels and yanked him forward. 

Sam stumbled, catching himself against Dean’s chest just as Dean raised his chin to meet his brother’s lips. Sam didn’t protest, just kissed back, easy and calm. Dean’s hands trailed down his body, skimming over his waist before dropping to squeeze his ass. Sam pulled away with a groan. 

“Subtle, Dean. Way to break it to him easy.” 

Cas was staring at them with something between confusion and disbelief. Dean met his gaze, eyebrows raised slightly. 

“Heaven’s spy network watching us our whole lives… we sorta just figured you knew.” 

“I had no idea,” Cas answered. His voice was a little rougher than usual; Dean chose to take that as a good sign. “How… since when…?” 

“Motels have two beds, man,” Dean answered, “Sammy and I bunked together ‘til I was almost fifteen.” 

“Three guys sharing a bathroom the size of a matchbox,” Sam added, rubbing at the back of his neck. “The boundaries just kinda… didn’t develop, you know?” 

“And then after Sammy died that first time, and I realized I didn’t have much time, we just sorta… stopped… worrying about it? I mean… we’re sorta beyond the ‘what are we’ talk at that point.” 

“And you feel that the two of you could include a third person in your lovemaking and have the experience remain unchanged?” 

Castiel was skeptical. The Winchesters exchanged a guilty glance. 

“If it was you?” Sam asked. Dean nodded. 

“We kinda already considered it. Just haven’t found a good time to bring it up.”

Cas blanched. 

“You must be joking.” 

Another pair of guilty glances. Cas looked from one brother to the other. Sam was looking at the floor. Dean was looking at Sam with a wicked grin. 

“Not kidding at all,” he answered. “Come on, Sammy, tell him what you wanted to do.” 

“Shut up, Dean,” Sam snapped, his face turning a little red. Dean was undeterred. 

“Well if you can’t tell, maybe you can show,” Dean suggested. He turned on his heel and near-skipped up the steps to the library, dropping heavily into a plush couch. His legs splayed wide, a clear invitation. Sam glanced to Cas. The angel stared at him through narrow eyes, like he suspected the humans might be playing a trick on him. 

Sam dropped his eyes and followed his brother up the stairs. When he reached the couch he dropped to his knees. His hands rested on Dean’s thighs. 

“Are you sure about this?” he whispered, hopefully quiet enough for Cas not to hear. Dean just grinned at him. 

“You worried the angel’s gonna think you’re a slut?” 

Sam scowled, but Dean’s face softened. He ran his hand through Sam’s hair, marveling at the softness he was definitely going to make fun of later. “Come on Sammy. Show him it’s okay.” 

Sam nodded and dropped his attention to the waistband of his brother’s pants. Dean looked back up to where Cas was still standing, nonplussed, in the main room. 

“C’mere, you’re gonna miss the show.” 

Cas came hesitantly up the stairs while Sam brought Dean’s soft cock out of his jeans. He took it into his mouth just as Cas reached them, drawing a low groan out of the elder brother. Dean’s head fell back, resting against the couch. 

“He’s blushing, but he loves it,” he told Cas, not even needing to look. He cracked an eye anyway. Cas was watching Sam, transfixed, his eyes the same panicked width that Dean had seen in the brothel, all those years ago. “Dude, calm down.” 

“I had no idea,” Cas breathed. He didn’t look away. Hesitantly he reached out, his fingers stopping only a few inches from Sam’s face. He froze, looking to Dean as though for confirmation. 

“You can touch him,” Dean affirmed. He watched as Cas brushed a strand of hair out of Sam’s face. Sam didn’t open his eyes, but there was an appreciative hum that went straight up Dean’s spine. His cock hardened a little further, enough that Sam could no longer fit the entire length into his mouth. 

“This is  _ half _ the fantasy he was telling me about, last time we did this,” Dean said. Hazel eyes flicked up to his face, but Sam trusted him to do this right. Dean looked to Cas. “If you’re game, I’ll tell you the other half.” 

Cas turned to look at him, his face still bearing traces of panic. 

“I believe I am… game,” he said after a minute. 

Dean responded by pulling his shirt over his head, taking his tee with it, leaving his torso bare. 

“Okay, you gotta at least lose the jacket, or this is going to be weird.” Dean tapped the top of Sam’s head. “You too, sweetheart.” 

Sam pulled off, wiping a strand of saliva from the corner of his mouth. 

“You’re a real dick sometimes, you know that?” he asked, standing as he yanked the flannel off his arms. 

Castiel paused, his overcoat discarded and his suit jacket halfway off his shoulders. 

“Is this upsetting you, Sam?”

“Just Dean being a cocky son of a bitch, that’s all.” 

Sam kicked out of his boots and started on his fly. Dean leaned forward, catching his wrist. 

“Not yet,” Dean said firmly, and again, the two of them shared a silent conversation. Sam looked to Cas. 

“It’s not upsetting me. You good?” 

Cas nodded. 

“I am both good and game,” he confirmed. He was fiddling with the bottom button on his untucked shirt, unsure if he should go further. Looking at the state of the other two, he decided that bare torsos were acceptable at this stage, and unbuttoned the shirt. 

The other two looked at him for a moment, and he thought he’d done something inappropriate until they glanced at each other and grinned. 

“What was the second half of the fantasy?” he asked, trying to circle the attention back around from himself. To his surprise, Sam turned and walked away, heading down the hallway in the direction of the bedrooms. 

“He’s just getting some paraphernalia,” Dean assured him. “He’ll be back.” 

Cas turned to look at the elder brother. 

“Dean, I need you to be certain that you are not doing this on my behalf. If you or Sam feel even the slightest bit uncomfortable with this, I’d rather spend an eternity in heaven than force you-”

“Nobody’s forcing us, Cas,” Dean interrupted. The sincere tone of his voice was at odds with the softening hardon sprouting from his jeans, but Castiel appreciated it anyway. 

Sam returned quickly, tossing a bottle to Dean when he got within range. Dean glanced at it, nodded, and turned back to Cas. 

“You ready?” 

Castiel swallowed hard, glancing to Sam. 

“Sam, I appreciate what you’re trying to do for me, and I want you to know that if you’re made to feel uncomfortable or want to stop-” 

Sam caught him by the chin, pressing their bodies flush. Cas let out an involuntary moan when Sam’s lips pressed to his, the evidence of the man’s arousal undeniable against Cas’s hip. Sam kissed him hard, nipping at his lower lip while his hands roamed over the angel’s bare skin. 

“I’m not uncomfortable,” Sam concluded when he eventually pulled away. He returned to the couch, where Dean had been lazily stroking himself as he watched.  

“Now  _ I’ve _ got a fantasy, _ ”  _ Dean muttered, watching his brother kneel again. This time, Sam popped the button on his jeans, pushing the zipper down before leaning in to rest his cheek on Dean’s thigh. 

“You’re up, Cas,” Dean said, groaning as Sam’s tongue flicked out to lap against his shaft. Castiel hesitated, but Dean waved him over, gesturing to the space behind Sam’s back. 

Cas knelt, watching the muscles of Sam’s back and shoulders moving beneath his skin. Gingerly, he let his hands rest on Sam’s hips, stroking lightly back and forth, getting used to the feeling of being allowed to touch. 

Dean leaned forward, reaching across Sam’s body to push at the hem of his pants. They slid easily down his thighs. Cas looked up, startled, to where Dean was grinning at him. 

“The fantasy was to have us both, Cas. At the same time.” 

Cas looked down, over the expanse of scarred skin now bared before him. Cautiously, he drew his hands down over Sam’s ass, down the inside of his thighs. Any second he expected one of the brothers to snap at him, berate him for some breach of etiquette or social faux pas, but neither of them spoke. Sam only groaned as Cas continued his exploration, palms rising to cup Sam’s balls. The skin there was soft, the hair coarse, and above them, Cas could feel the hard base of Sam’s erection. He let his fingers skim up the length of it, stopping when he reached a bead of moisture at the head of Sam’s cock. 

“God, yes, Cas,” Sam murmured. He’d paused his activities to pay attention to what the angel was doing, and now he looked back over his shoulder. “Please. I can’t even tell you how bad I want this.” 

“Want…?” Cas asked, but Dean was pushing Sam’s head back down, picking up the conversation himself. 

“He wants you in his ass, while he’s blowing me, so he can feel both of us fucking him at the same time. Get it?” 

Cas couldn’t tell if he got pale or blushed. Dean was grinning at him and Sam’s cock even twitched a little at the lewd suggestion. 

“That would… certainly go against the rules of heaven…” Cas said weakly, but Dean shook his head. He leaned forward, making sure Cas could see his fingertip circling Sam’s pink hole. 

“Yeah, but he wanted it  _ before _ that,” Dean leered. Cas saw something wet on Dean’s fingertips, and realized he must have opened the bottle that Sam brought him. 

Dean slid a wet finger into Sam’s hole, and Sam groaned, the sound muffled around the girth of Dean’s cock. 

“C’mere, Cas. Feel,” Dean urged, slowly fucking a long finger in and out of his brother’s ass. “There’s room. I promise.” 

His voice was coarse, the desire obvious on his face as Cas considered. 

The seraph reached out, one fingertip circling the circle of muscle around Dean’s knuckle. He almost glanced to Dean again, looking for permission, but he managed to stop himself. Instead he pressed forward, surprised at how little effort it took for Sam’s body to accommodate the intrusion. Only the slightest pressure and he was inside, the slick hot velvet of Sam’s body enveloping him. 

“ _ Oh, _ ” Cas heard himself whisper, and Dean chuckled. Sam rolled his hips backward, taking them deeper.

“Feels nice, doesn’t it?” Dean asked, and Cas could only nod, staring mutely at their entwined fingers. “Imagine how that’ll feel on your cock.” 

“ _ Oh, _ ” Cas repeated, a little weaker. As he watched, Dean added another finger, twisting them inside, against Sam’s hole. 

“You hard yet?” the hunter asked him, and Cas nodded weakly. Dean withdrew, leaving Sam with only Castiel’s single digit. Sam made a disappointed noise. 

“See if you can get three in,” Dean instructed Cas, upending the bottle and letting slippery lube drip over the angel’s fingers. 

Cas compiled, a little surprised at how easily Sam adjusted to accept him. He worked his fingers in and out, watching Sam stretch around them. 

Sam whimpered. 

“ _ Please, _ Cas,” he mumbled into Dean’s thigh. Cas looked to Dean, whether for confirmation or permission, he didn’t know. Dean nodded. 

With unsteady fingers, Cas unzipped his slacks, letting his cock spring free. He hadn’t realized how uncomfortable it had been. 

He stroked himself twice, letting the excess lube coat his shaft. Sam was watching over his shoulder, eyes widening a little when he saw the angel touching himself. 

“Fuck, yeah,” he started to say, but Dean pushed his head back down before he could go further. 

“Shoulda gone with four,” Dean muttered, looking Cas over. “Don’t tease him, man. Do it.” 

Cas ran a hand up the small of Sam’s back, noting the shiver of anticipation. Once more, he considered asking if Sam was sure, but a look at Dean’s face gave him the answer he needed. 

He pressed the head of his cock against Sam’s stretched hole, pushing in an inch at a time. Sam moaned around Dean’s cock, his fingers tightening on Dean’s thighs. Cas paused. 

“Am I going too fast?” 

Dean shook his head, staring at Cas’s cock where it disappeared inside his little brother.

“Nah. He’s fine. Fill him up, Cas.” 

Cas paused a moment, and when Sam made no comment to the contrary, he pushed forward again. This time he didn’t stop until he was fully sheathed, his hips rocking forward against the back of Sam’s thighs. Sam groaned, his nails scratching against the top of Dean’s legs. 

Cas withdrew and pushed forward again, just an inch, testing the waters. The two humans made simultaneous noises as the motion pushed Sam down further against Dean’s cock. 

“Do that again,” Dean ordered when he’d caught his breath. 

Cas repeated the motion, his own fingers tightening on Sam’s hips as the tight heat of the hunter’s body enveloped him. 

“ _ Harder, _ ” Sam demanded, and when Cas hesitated he took the initiative himself, pushing back hard against the angel, fucking himself on Castiel’s cock. All Cas could do was hold still, watching enraptured as Sam oscillated between the two of them, swallowing Dean down and then pulling back to impale himself on Cas. 

“That’s right, Sammy, such a  _ slut _ for it,” Dean crooned. His fingers were tangled in Sam’s hair, not pulling, just holding. “You like that? Like being stuffed full at both ends?” 

Sam groaned, sending a ripple of vibration through his throat, effectively shutting Dean up. 

Cas had his eyes closed, so he didn’t see Dean’s fingers tightening in Sam’s hair, pulling the younger man back. He didn’t see Dean taking hold of his own shaft, stripping it rapidly until he came with a groan. 

Cas opened his eyes when a stripe of come landed across his collarbone. He looked down, startled, and the next landed across his cheek. 

He watched, still buried inside Sam, as Dean’s come splattered across both of them, first on Cas’s chest and belly, then on Sam’s back and shoulders as the spurts got weaker. The last landed neatly in Sam’s waiting mouth, coating his tongue. 

Cas forgot how to breathe. 

 


	2. Chapter 2

**Notes for the Chapter:**

> This chapter has Dean/Cas in it.

Dean leaned back against the couch, looking at the spread before him with satisfaction. Cas had slowed his thrusts, pushing into Sam almost distractedly. His focus was on his fingertips, trailing through the wet mess on his shoulder and chin. 

Dean approved of this. 

“Got some onanism in there, to round off the pot,” Dean explained, when Cas looked at him. Cas shook his head. 

“That was an extremely specific set of circumstances, for the general population-”

“Save the history lesson,” Dean interrupted. Sam’s forehead was furrowing in a way that indicated they didn’t have much time. “Is that gonna do it? Like is that enough to ward off the god squad or does Sammy have to paint you, too?” 

Cas’s mouth fell open, but he quickly regained his composure. 

“Sam’s effluence would certainly… contribute to the effect…”

“You better pull out, then,” Sam groaned, leaning forward. Cas was left kneeling, his erection bobbing weakly in nothing but air. 

“You wanna lie on the couch?” Sam asked, looking at him. “I can ride you the rest of the way.” 

Cas opened his mouth again, this time looking down. 

“I think it might be most effective if… if I were to be the recipient in this exchange.” His eyes darted to Sam. “If you don’t object?” 

Dean and Sam exchanged glances. 

“That… might have worked better with Dean…” 

Castiel’s eyes widened as Sam shimmied out of his jeans. His cock was  _ thick, _ and as Cas watched, Sam palmed himself into full hardness, adding at least another inch to the length. Cas felt something lurch in his stomach- something between anticipation and fear. 

Cas reached out, his fingers brushing Sam’s as he wrapped his hand around the hunter’s shaft. He stroked, twice, getting the feel for it. 

“I’d like to try,” he said, with more confidence than he felt. 

Dean watched the two of them have a silent conversation, a little surprised to find his cock filling again at the image of the angel taking his brother’s dick.  

He shoved off the couch, letting Sam take his place. The two hunters watched Cas undressing, kicking off his slacks and standing naked in front of them for the first time. 

He wasn’t as skinny as Dean had always pictured. 

Sam beckoned to him and Cas climbed, a little awkwardly, to straddle his thighs. 

Sam looked him over, his fingers tracing the wet lines Dean had left. He rubbed it in, starting low and working up, until his hand was cupping Cas’s jaw. 

Dean could see the shiver rippling down Cas’s back, making his hair stand on end. The angel was chest-to-chest with Sam, his hands resting on the back of the couch. While Dean finished undressing, Sam ran his hands down Cas’s sides, over his thighs, calming him. One hand reached for the lube, but Dean caught it, kneeling behind Cas. 

“Lean forward,” Dean instructed, and Cas did. 

Sam mouthed at the junction of his throat, seeking out the lines of salt, leaving red marks that Dean suspected he’d see again tomorrow. For right now, he wasn’t looking at them. He was looking at Cas’s virgin hole, helpfully spread and displayed for him. He ran his thumb over the puckered orifice, listening to Cas’s answering hiss. 

“Relax,” he said quietly, and before Cas could react, Dean leaned in, replacing the pad of his thumb with the tip of his tongue. 

Sam had anticipated this, so when Cas jumped, he didn’t go far. Sam’s hands were on his hips, keeping him still. 

“Dean! You can’t-” 

“This is the whole point, isn’t it?” Sam interrupted, the words spoken soft in Cas’s ear. Dean didn’t slow down, and Cas’s answer was shaky when it came. 

“It furthers our goal, but-  _ oh-  _ but I can’t ask… I don’t expect…” 

“You’re not asking,” Sam told him. He continued leaving bites along the column of Cas’s throat, cupping his ass and pulling the angel’s cheeks wider. “He’s good, though, isn’t he?” 

Cas answered with a small whimper, and a tensing of his muscles that let Sam know that Dean had breached him. 

“That’s one,” Sam told him. “If you’re serious about this, he’ll probably have to go up to four.” 

Cas didn’t respond, just nodded against Sam’s shoulder. Dean saw and reached for the lube, twisting his spit-slick finger inside Cas’s twitching hole. 

“This might be cold,” Dean warned. A moment later, Cas shuddered as a second finger entered him. His arms tightened around Sam’s back, his face still buried in Sam’s shoulder. Sam’s fingers stroked down his spine, over his ribs and sides. Cas was making helpless little noises, his body trembling with the onslaught. 

“Relax, we’ve got you,” Sam murmured. Cas shook his head, not looking up. 

“I’m trying,” he answered. His voice was rough, enough that Dean paused and looked up. “I’m sorry, I’m trying.” 

“Don’t try so hard. It’s supposed to feel good.” 

Dean watched as Sam caught Cas’s jaw, drawing him up into a deep kiss. Almost immediately, Cas loosened around Dean’s fingers. Dean didn’t add another one, just kept scissoring him open with the two already inserted. He was getting an idea, but he’d need to leave the room to get what he needed and at the moment, he was unwilling to do that. 

Cas’s back arched, spreading his ass a little further, and Dean couldn’t help himself. He added a third finger, and Cas accommodated him easily, taking the extra digit without issue. 

“That good?” he asked, and Cas only whimpered the affirmative. Dean’s free hand dropped between his legs, palming his renewed erection. 

“Think you’d like to try a toy, Cas?” he asked, and damn if that didn’t make  _ Sam _ jerk. “I’ve got one I use to prep myself for Sam.” 

Cas looked to Sam, like he was looking for approval, and Sam nodded. 

Dean withdrew, wiping his fingers on a piece of discarded clothing. Sam watched him go, almost preoccupied with massaging the globes of Cas’s ass. 

It took Dean less than a minute to find the toy and return, and by that time Cas was leaning back, his hands around Sam’s shoulders, while Sam jacked the two of them in tandem. Cas was panting, his eyes closed, and Dean had to catch his jaw to get his attention. 

He held the toy up where Castiel could see it. It was a bluish glass dildo, ridged and pebbled, tapering ever so slightly from the base. Cas’s eyes widened and he swallowed deeply. 

“I’ll go slow,” Dean promised, and Cas nodded. He leaned forward again, his thighs spreading, giving Dean access to his hole. 

Sam cupped his ass, spreading him wider, letting Dean see how much the pink little rosebud had already closed up in the time he’d been gone. 

“Touch yourself, Cas,” Sam told him, his lips brushing against Cas’s ear. 

Cas obeyed, dropping his hand between the two of them, tentatively stroking his flagging cock. 

Dean applied more lube and lined the blunt head of the toy up against Cas’s hole. 

“Breathe,” Sam reminded him, and Cas took a deep gasp as the toy penetrated him, sliding several inches into his stretched ass. 

“Perfect,” Sam crooned, and leaned in for another kiss. 

He kept Cas occupied, kissing him and making sure the angel never stopped stroking himself, while Dean worked the toy deeper and deeper into Cas’s hole. A few times the angel tensed, gasping, a fine sheen forming on his skin. When this happened Dean paused, stroking his fingers up Cas’s spine, withdrawing the last inch of the toy and twisting the pebbled length inside Cas. 

When the flared base of the toy was slotted up against Cas’s rim, Dean glanced up, catching Sam’s eye and nodding. 

Sam reached between himself and Cas, taking both of their cocks and stroking in unison. 

“Is that still good?” Sam asked, nipping at Cas’s ear. The angel nodded, his face buried in Sam’s shoulder. 

“Use your words,” Dean prompted. 

“Yes, it’s g-  _ ah! _ ” Cas exclaimed. Dean rotated the toy a little more, loving how the seraph trembled at the feeling of the nubs inside his body. 

“We’re gonna get you one that vibrates,” Dean said definitively. 

“Later,” Sam interjected. He reached for the lube, snapping it open and letting a few drops land against his slit. Cas watched, eyes wide, as the clear drops made their way down Sam’s shaft. Sam grinned and took his hand, wrapping it around the slick shaft. Cas was a quick learner, and he began to stroke, smearing the lube over the head and shaft. 

“Think you can take that?” Sam asked. Cas nodded again, unwilling to try speaking while Dean was still fucking him open with the glass toy. 

Dean leaned back, withdrawing the toy inch by inch, leaving Cas empty and whimpering. He set it to the side, sitting back and taking in the view. 

“Up on your knees, Cas,” Sam said, lifting gently to show the angel what he wanted. Cas rose up, his knees still wide, positioning himself above Sam. From his place on the floor, Dean could see his worked-open hole, still slick with lube. As he watched, Cas lowered himself a fraction, letting the head of Sam’s cock rest against his entrance. 

“Just like that, go slow,” Dean suggested. Cas looked back at him, noticing for the first time that Dean was jerking himself lazily. 

“Ignore him,” Sam said. “Look at me. I’ve got you.” 

He raised his knees, giving Cas something to lean against. Cas took a deep breath, letting it out slowly as he sank down onto Sam’s length, letting it breach him before freezing. Sam could feel him flinch, his body tightening abruptly around the head of Sam’s cock.

“I can’t-” 

“It’s fine. You’re fine. Give yourself a second to adjust.” 

Sam let his hands slip around Cas’s shoulders, stroking the muscles of his back. He could feel the angel relaxing, slowly, slipping a millimeter further down. He was almost painfully tight, even with the prep, and Sam could only imagine what it would be like to be buried all the way inside him. 

On the floor, Dean sat with his legs spread, watching Cas working himself down onto Sam’s cock. He could remember the first time he’d taken it from Sam- he’d done it on all fours, his hands fisted in the sheets while his brother fucked into him from behind. 

Cas’s breath was coming ragged. The stretch and burn in his hole was like nothing he’d felt in a vessel before. It had been extremely pleasurable when Dean had used his fingers and the toy, but this was bigger than either of those. Each time he sank down further onto it, he was sure that he had reached his limit, that he would be unable to continue. He’d hold, breathing slow, feeling the hunter’s firm grip on him, and he’d wait. 

And sure enough, little by little, his body would adjust. He’d expand to accommodate the penetration, and he’d take a little more. 

He was determined to do this. If Sam and Dean thought that he belonged here, if they wanted him in their beds, then he would prove that he was up to it. 

As if to accentuate the thought, he slid the final two inches, making a soft, pained noise as he felt Sam bottoming out inside him. He was utterly still, his thighs bracketing Sam’s hips, his fingers gouging divots in the hunter’s shoulders. 

“Please… do not move,” he murmured. His eyes were closed, his forehead furrowed as he tried to relax his vessel. 

“I’m not going anywhere,” Sam answered, and Cas felt something twist in his stomach at the gentle tone of the man’s voice. His hands were still on Cas’s back, stroking the tensed muscles there. 

“It is… more difficult than I expected,” Cas admitted. He was still unwilling to look at Sam, though behind him, he could hear Dean expressing his appreciation for the view. 

“Hard part’s over,” Sam reminded him. He let one hand rest on Cas’s hip, while the other shifted to stroke over the angel’s softened cock. “Want me to help you with that?” 

Cas paused, considered, and nodded. His vessel was sending him warning signals, letting him know to tread softly now. He wasn’t sure he’d be able to become erect in such a condition, but evidently Sam knew what he was talking about. Within a minute, Cas’s cock was hard and leaking between them. 

“You feel so damn good around me,” Sam murmured in his ear, and Cas shivered. “Every time I stroke you, you squeeze me like you’re afraid I’ll pull out. Did you know you were doing that?” 

“No,” Cas whimpered. He was still hesitant to move, though the pain of penetration had lessened somewhat. He felt like he should be doing something in return, but he was at a loss as to what. 

Sam took the initiative instead, reaching up with his free hand to pinch one of Cas’s nipples. Cas arched involuntarily, letting out a cry. 

“God, yeah, just like that,” Sam urged, his hand moving faster over Cas’s cock. Cas angled his hips, trying to give Sam better leverage, and suddenly there was something  _ inside _ him sending sparks up his spine- 

Cas rocked his hips again, rising slightly off Sam and settling back down, chasing those sparks, and Sam groaned. 

“Fuck, you’re tight,” he muttered, gasping as Cas rocked against him again. “Like you’re trying to squeeze the come right out of me.” 

Cas got bold, rising up a little further and dropping back down onto Sam’s hips. The sparks shot up his spine and he knew how to do it now, it was right  _ there- _

“That what you want?” Sam panted, trying to keep his hands in time with Cas’s movements. “Want my come in you, filling up that tight hole of yours?” 

“ _ Yes!”  _ Cas groaned, and almost instantly, Dean was treated to the sight of white come leaking from Cas’s hole. It was almost enough to set him off and he surged up, taking Cas by the shoulder and pulling back. Sam saw immediately what he was up to and braced against Cas’s knees. The angel was left flat on his back, looking up at Dean, his cock rising obscenely into the air. 

“Open your mouth,” Dean grunted, and Cas did, closing his eyes just as Dean’s second release splattered over his lips and tongue. A moment later Cas was coming himself, painting his chest and belly with his own semen. 

Dean moved his hips, letting the wet end of his cock stroke against Cas’s face, smearing his come over the angel’s cheeks and lips and chin. When he looked over, Sam was playing with Cas’s nipples, teasing them into peaks, shiny with come. 

“Look at you, all fucked out and debauched,” Dean mused. Cas cracked an eye. 

“Am I?” 

“Oh yeah,” Sam confirmed. He was smearing a drop of come into Cas’s belly button. “You’re filthy.” 

“Think we should call Gabe?” Dean asked. “He could probably tell whether that was enough.” 

“No,” Cas said emphatically. Dean looked down at him and Cas tilted his chin up, his tongue running along the wet underside of Dean’s cock. “Let’s give it another day, before we bother him.” 

Sam laughed. 

**Notes for the Chapter:**

> I totally fucked up the prompts. Nobody gets what they wanted. Fuckit. 
> 
>  
> 
> Smol Bean kept fidgeting while I was writing this. This is what I'm exposing her to in utero. She has no chance.

**Author's Note:**

> Chapter two... someday.... 
> 
>  
> 
> 365 still on hiatus. I can't write overwhelming dissociation and hopelessness unless I'm otherwise mostly happy and... well.   
> Fuck Trump.


End file.
